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$138+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Round-trip from

$223
(Delta)

One-way from

$138
(Delta)

Popular in

December

Cheapest in

April

Average price

$268
From Calgary to Chicago Midway
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One-way flight from Calgary to Chicago Midway
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Highest demand for flights based on searches. 24% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:40 amYYC - MDW
1 stop9h 55mDelta
Tue 10/79:35 amMDW - YYC
2 stops12h 12mDelta
Deal found 8/15$223
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:40 amYYC - MDW
1 stop9h 55mDelta
Wed 10/89:35 amMDW - YYC
2 stops12h 12mDelta
Deal found 8/17$243
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2912:30 amYYC - MDW
1 stop14h 28mMultiple Airlines
Tue 10/78:05 amMDW - YYC
1 stop12h 55mMultiple Airlines
Deal found 8/15$261
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/212:30 amYYC - MDW
1 stop12h 31mMultiple Airlines
Thu 9/46:20 amMDW - YYC
1 stop14h 40mMultiple Airlines
Deal found 8/17$285
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:00 amYYC - MDW
2 stops15h 25mMultiple Airlines
Sun 10/196:20 amMDW - YYC
1 stop14h 40mMultiple Airlines
Deal found 8/15$293
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2812:30 amYYC - MDW
1 stop14h 30mMultiple Airlines
Sun 10/56:20 amMDW - YYC
1 stop14h 40mMultiple Airlines
Deal found 8/17$303
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:40 amYYC - MDW
1 stop9h 55mDelta
Sun 10/59:35 amMDW - YYC
1 stop9h 49mDelta
Deal found 8/17$313
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/127:00 amYYC - MDW
2 stops15h 25mMultiple Airlines
Fri 10/179:44 amMDW - YYC
1 stop11h 16mMultiple Airlines
Deal found 8/15$314
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:55 amYYC - MDW
1 stop13h 10mMultiple Airlines
Mon 12/156:00 amMDW - YYC
1 stop14h 09mMultiple Airlines
Deal found 8/17$343

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/30

6:40 am-5:35 pm

1 stop9h 55m

Chicago Midway

Tue 10/7

9:35 am-8:47 pm

2 stops12h 12m

$223

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/1

6:40 am-5:35 pm

1 stop9h 55m

Chicago Midway

Wed 10/8

9:35 am-8:47 pm

2 stops12h 12m

$243

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 9/29

12:30 am-3:58 pm

1 stop14h 28m

Chicago Midway

Tue 10/7

8:05 am-8:00 pm

1 stop12h 55m

$261

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/2

12:30 am-2:01 pm

1 stop12h 31m

Chicago Midway

Thu 9/4

6:20 am-8:00 pm

1 stop14h 40m

$285

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 9/28

12:30 am-4:00 pm

1 stop14h 30m

Chicago Midway

Sun 10/5

6:20 am-8:00 pm

1 stop14h 40m

$285

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 10/17

7:00 am-11:25 pm

2 stops15h 25m

Chicago Midway

Sun 10/19

6:20 am-8:00 pm

1 stop14h 40m

$293

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 9/29

6:40 am-5:35 pm

1 stop9h 55m

Chicago Midway

Sun 10/5

9:35 am-6:24 pm

1 stop9h 49m

$313

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 10/4

6:40 am-1:03 pm

1 stop5h 23m

$138

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 11/24

6:35 am-1:09 pm

1 stop5h 34m

$138

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 11/19

6:35 am-1:09 pm

1 stop5h 34m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 15 results
1
2

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Calgary to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of $160). Flying from Calgary to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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